diff --git a/docker/Dockerfile.agent.windows.1803 b/docker/Dockerfile.agent.windows.1803
index f1256b458..3368be0df 100644
--- a/docker/Dockerfile.agent.windows.1803
+++ b/docker/Dockerfile.agent.windows.1803
@@ -1,4 +1,4 @@
-FROM microsoft/nanoserver:1803
+FROM mcr.microsoft.com/windows/nanoserver:1803
 USER ContainerAdministrator
 
 ENV GODEBUG=netdns=go
@@ -8,5 +8,5 @@ ENV DRONE_RUNNER_PLATFORM=windows/amd64
 ENV DRONE_RUNNER_KERNEL=1803
 ENV DRONE_RUNNER_CAPACITY=1
 
-ADD release/windows/amd64/drone-agent.exe /drone-agent.exe
-ENTRYPOINT [ "\\drone-agent.exe" ]
+ADD release/windows/amd64/drone-agent.exe C:/drone-agent.exe
+ENTRYPOINT [ "C:\\drone-agent.exe" ]
diff --git a/docker/Dockerfile.agent.windows.1709 b/docker/Dockerfile.agent.windows.1809
similarity index 50%
rename from docker/Dockerfile.agent.windows.1709
rename to docker/Dockerfile.agent.windows.1809
index 985c765bb..05cb02e2b 100644
--- a/docker/Dockerfile.agent.windows.1709
+++ b/docker/Dockerfile.agent.windows.1809
@@ -1,12 +1,12 @@
-FROM microsoft/nanoserver:1709
+FROM mcr.microsoft.com/windows/nanoserver:1809
 USER ContainerAdministrator
 
 ENV GODEBUG=netdns=go
 ENV DRONE_RUNNER_OS=windows
 ENV DRONE_RUNNER_ARCH=amd64
 ENV DRONE_RUNNER_PLATFORM=windows/amd64
-ENV DRONE_RUNNER_KERNEL=1709
+ENV DRONE_RUNNER_KERNEL=1809
 ENV DRONE_RUNNER_CAPACITY=1
 
-ADD release/windows/amd64/drone-agent.exe /drone-agent.exe
-ENTRYPOINT [ "\\drone-agent.exe" ]
+ADD release/windows/amd64/drone-agent.exe C:/drone-agent.exe
+ENTRYPOINT [ "C:\\drone-agent.exe" ]
diff --git a/docker/Dockerfile.controller.windows.1803 b/docker/Dockerfile.controller.windows.1803
index ff607a6c3..be1e563ad 100644
--- a/docker/Dockerfile.controller.windows.1803
+++ b/docker/Dockerfile.controller.windows.1803
@@ -1,4 +1,4 @@
-FROM microsoft/nanoserver:1803
+FROM mcr.microsoft.com/windows/nanoserver:1803
 USER ContainerAdministrator
 
 ENV GODEBUG=netdns=go
@@ -8,5 +8,5 @@ ENV DRONE_RUNNER_PLATFORM=windows/amd64
 ENV DRONE_RUNNER_KERNEL=1803
 ENV DRONE_RUNNER_CAPACITY=1
 
-ADD release/windows/amd64/drone-controller.exe /drone-controller.exe
-ENTRYPOINT [ "\\drone-controller.exe" ]
+ADD release/windows/amd64/drone-controller.exe C:/drone-controller.exe
+ENTRYPOINT [ "C:\\drone-controller.exe" ]
diff --git a/docker/Dockerfile.controller.windows.1809 b/docker/Dockerfile.controller.windows.1809
new file mode 100644
index 000000000..98609ed30
--- /dev/null
+++ b/docker/Dockerfile.controller.windows.1809
@@ -0,0 +1,12 @@
+FROM mcr.microsoft.com/windows/nanoserver:1809
+USER ContainerAdministrator
+
+ENV GODEBUG=netdns=go
+ENV DRONE_RUNNER_OS=windows
+ENV DRONE_RUNNER_ARCH=amd64
+ENV DRONE_RUNNER_PLATFORM=windows/amd64
+ENV DRONE_RUNNER_KERNEL=1809
+ENV DRONE_RUNNER_CAPACITY=1
+
+ADD release/windows/amd64/drone-controller.exe C:/drone-controller.exe
+ENTRYPOINT [ "C:\\drone-controller.exe" ]
diff --git a/docker/manifest.agent.tmpl b/docker/manifest.agent.tmpl
index 0bfcfde65..43e2f43bf 100644
--- a/docker/manifest.agent.tmpl
+++ b/docker/manifest.agent.tmpl
@@ -24,7 +24,13 @@ manifests:
       os: linux
       variant: v7
   -
-    image: drone/agent:{{#if build.tag}}{{trimPrefix "v" build.tag}}-{{/if}}windows-amd64
+    image: drone/agent:{{#if build.tag}}{{trimPrefix "v" build.tag}}-{{/if}}windows-1803
+    platform:
+      architecture: amd64
+      os: windows
+      variant: 1803
+  -
+    image: drone/agent:{{#if build.tag}}{{trimPrefix "v" build.tag}}-{{/if}}windows-1809
     platform:
       architecture: amd64
       os: windows
diff --git a/docker/manifest.controller.tmpl b/docker/manifest.controller.tmpl
index f7cb5a7d9..7ee4ff6f0 100644
--- a/docker/manifest.controller.tmpl
+++ b/docker/manifest.controller.tmpl
@@ -24,8 +24,14 @@ manifests:
       os: linux
       variant: v7
   -
-    image: drone/controller:{{#if build.tag}}{{trimPrefix "v" build.tag}}-{{/if}}windows-amd64
+    image: drone/controller:{{#if build.tag}}{{trimPrefix "v" build.tag}}-{{/if}}windows-1803
     platform:
       architecture: amd64
       os: windows
       variant: 1803
+  -
+    image: drone/controller:{{#if build.tag}}{{trimPrefix "v" build.tag}}-{{/if}}windows-1809
+    platform:
+      architecture: amd64
+      os: windows
+      variant: 1809